12 Terry Dr · Shelter Island, NY 11964

$2,950,000

5 bd · 4.5 ba · 4,200 sqft · SingleFamily · 72 Days on market

Built 2016 Good condition 0.50 ac lot $702/sqft · 34% below area Est $4459k · 34% under $15/mo HOA

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Why this score? — see what drove the A- grade

The composite is a weighted blend of 9 inputs, each scored 0–100. Each bar is that input's sub-score; the figure is the points it added to the 100-point composite (weight × sub-score).

• Cash flow +30.0/30.0
• ARV discount +15.0/15.0
• 1% rule +10.0/10.0
• DSCR +10.0/10.0
• Appreciation +6.0/10.0
• Schools +4.1/10.0
• Condition / age +4.0/5.0
• Livability +3.0/5.0
• Rent growth +2.5/5.0

Listing remarks MLS

Located in the desirable Harborview area of Shelter Island, this modern farmhouse blends luxury, comfort, and coastal living. Just 0.2 miles from a private waterfront association, enjoy easy access to kayaking and the beach. Set on a beautifully landscaped half acre, the home is designed for seamless indoor-outdoor living. The open-concept interior is flooded with natural light, featuring a chef’s kitchen that flows effortlessly to the dining and living areas, highlighting views of the backyard oasis. Outside, relax in the heated pool, outdoor shower, or firepit lounge, or entertain on the spacious deck with retractable awning and covered dining area. With five generous bedrooms, including primary suites on both the first and second floors, the home accommodates guests in style. The upstairs suite features a gas fireplace and covered balcony. The fully finished lower level includes a media room with theater seating, a versatile den or gym with yard access, and a fifth bedroom with a large hall bath. Step inside and start enjoying the best of Shelter Island living.

Key facts

• 0.5 acre lot
• 2 garage spots
• Pool

What this means for you Summary

Snapshot

• This is a 5-bed/4.5-bath single-family listed at $2.95M. Condition is rated good.

Deal economics

• At list price, monthly cash flow is $22k ($261k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($53k rent vs $2.95M).
• Recommended offer: $2.77M (6.0% below list) — sets the bar for market timing.

Location & tenants

• Location reads 60/100 on livability (#998 in NY) — a middle-class / working-renter tenant base. Strengths: crime A+, employment A+; Watch: amenities F, commute F, cost of living F.
• Shelter Island Union Free School District (rural): math 40% / reading 45% proficiency, ranked #546 of 755 in NY (top 72%) — families likely to look elsewhere, expect single-tenant / working-renter base with shorter leases; only 16% free/reduced lunch — higher-income household profile.
• Market conditions: 39 active listings in the ZIP; 3 comparable units currently listed for rent nearby; rentals at typical pace (median 22d on market — plan ~3-4 weeks tenant-placement turnaround); 1,366 units permitted in Suffolk County in 2024 (216 in 5+ unit buildings).

Forward outlook

• In year one you build about $78k of equity ($20k loan paydown + $58k appreciation (2.0% local appreciation)).
• Suffolk County population projected to shrink 5% by 2050 — rents likely to lag national; underwrite the cash flow, not the appreciation.
• At projected returns (2.0% appreciation + 3.0% rent growth), your $826k cash investment doubles in ~3 years — after that, you're playing with house money.
• By year 3, paydown + projected appreciation supports a ~$199k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Negotiation context

• It's been on market 72 days — a 6% lower offer ($2.77M) is reasonable based on typical stale-listing flexibility.

Risks & watch-outs

• Climate carrying-cost: severe wind risk, 80% chance of damaging wind over 30y; extreme-heat days projected 7→19/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $2,773,000 (6.0% below list)

Questions for the listing agent

1. It's been on market 72 days. Have you received any prior offers? Is the seller open to a 6% concession, seller financing, or rate buy-down credit?
2. What does the HOA fee cover, when was the last increase, and are there any pending special assessments or reserve-fund shortfalls?
3. Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
4. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
5. What's the average days-on-market for RENTAL listings here right now (not sales)? A rising rental-DOM trend means longer vacancies and softer asking-rent achievability than the comps imply.
6. What's the recent tenant-quality profile in this submarket — average credit score on applications, eviction rate, late-payment / NSF rate, and stable-employment percentage? A property-management company in the area should have these aggregated.
7. How much new for-sale + rental construction is in the pipeline within 1–3 miles? Heavy new supply typically softens prices + rents 12–24 months out; constrained supply supports both.

Investment metrics

• 1% rule: 1.81% ✓
• Cap rate: 15.14%
• Cash-on-cash: 31.61%
• DSCR: 2.41
• GRM: 4.6

CMA / ARV

• ARV (median comp): $4,459,210
• List price: $2,950,000
• Delta: -33.84%
• Verdict: UNDERPRICED
• Comps: 6 within 1.0 mi

Show comp detail 2 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
8 Gardiner Way and 15a Harbor Ln	0.00mi	5/3.5	4,053 (-4%)	6mo	$4,997,500	$1,233	85
8 Cove Way	0.70mi	4/4.5 (-1)	3,676 (-12%)	2mo	$4,075,000	$1,109	40

Match score weights: distance 35% · size 25% · config 20% · recency 20%. Top-matched comps best support the ARV.

Projected returns pro-forma

1.97% appreciation · 3.0% rent growth · sell at horizon

5-year hold

• IRR: 35.7%
• Equity multiple: 2.92×
• Total profit: $1,583,984
• Equity at exit: $1,158,601

10-year hold

• IRR: 36.8%
• Equity multiple: 5.73×
• Total profit: $3,903,413
• Equity at exit: $1,664,604

Cash invested: $826,000 (down + closing). Projections, not guarantees.

Landlord ↔ Tenant lean methodology

• Overall (STATE): 15 Strongly Tenant-Friendly
• State New York: 15 Strongly Tenant-Friendly · D+10
• County: — inherits STATE
• City: — inherits STATE

NYC rent stabilization (~1M units); 2019 HSTPA strengthened tenant rights; courts deeply backlogged.

Methodology + full state rankings →

ZIP-level market 11964

• Home prices YoY: 0.4%
• Active inventory: 39
• Price-to-rent: 4.6×

Monthly cashflow live

• Estimated rent: $53,363 medium
• Mortgage (P&I): −$15,470
• Tax est. 1.5%: −$3,688 /mo · $44,250/yr
• Insurance: −$1,229
• HOA: −$15
• Vacancy / Maint / Mgmt: −$11,206
• Net cashflow: $21,755

Break-even live

Break-even rent $25,825

Max offer price $2,950,000

Occupancy floor 54%

UW: 25.0% down · 7.5% · 30yr · 1.5% tax · 5.0% vac · 8.0% maint · 8.0% mgmt

Financing live

Cash to close

• Down payment: $737,500
• Closing costs: $88,500
• Reserves months: —
• Total cash needed: —

Rent comps 3 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
15 Montclair Ave Shelter Island, NY	6.0	4.5	4600	$75,000	$16.30	22d	1	0.70mi
47L S Ferry Rd Shelter Island, NY	4.0	3.5	3800	$50,000	$13.16	22d	1	0.87mi
42 N Menantic Rd Shelter Island, NY	4.0	2.5	2825	$7,500	$2.65	43d	1	1.26mi

HOA detail

• Monthly dues: $15 · $180/yr
• Likely covers: watergaspoolgym

Listing history 16 events

1. 2026-06-18
   days on market $2,950,000 Active 72 DOM
2. 2026-06-17
   days on market $2,950,000 Active 71 DOM
3. 2026-06-16
   days on market $2,950,000 Active 70 DOM
4. 2026-06-15
   days on market $2,950,000 Active 69 DOM
5. 2026-06-13
   days on market $2,950,000 Active 67 DOM
6. 2026-06-13
   days on market $2,950,000 Active 66 DOM
7. 2026-06-09
   days on market $2,950,000 Active 63 DOM
8. 2026-06-08
   days on market $2,950,000 Active 62 DOM
9. 2026-06-07
   days on market $2,950,000 Active 61 DOM
10. 2026-06-04
    days on market $2,950,000 Active 58 DOM
11. 2026-06-03
    days on market $2,950,000 Active 57 DOM
12. 2026-06-02
    days on market $2,950,000 Active 56 DOM
13. 2026-06-01
    days on market $2,950,000 Active 55 DOM
14. 2026-05-31
    days on market $2,950,000 Active 54 DOM
15. 2026-04-08
    listed $2,950,000 Active 1086-char remark

    Show marketing remark (1086 chars)

    Located in the desirable Harborview area of Shelter Island, this modern farmhouse blends luxury, comfort, and coastal living. Just 0.2 miles from a private waterfront association, enjoy easy access to kayaking and the beach. Set on a beautifully landscaped half acre, the home is designed for seamless indoor-outdoor living. The open-concept interior is flooded with natural light, featuring a chef’s kitchen that flows effortlessly to the dining and living areas, highlighting views of the backyard oasis. Outside, relax in the heated pool, outdoor shower, or firepit lounge, or entertain on the spacious deck with retractable awning and covered dining area. With five generous bedrooms, including primary suites on both the first and second floors, the home accommodates guests in style. The upstairs suite features a gas fireplace and covered balcony. The fully finished lower level includes a media room with theater seating, a versatile den or gym with yard access, and a fifth bedroom with a large hall bath. Step inside and start enjoying the best of Shelter Island living.

16. 2026-04-02
    historical $2,950,000 1086-char remark

    Show marketing remark (1086 chars)

    Located in the desirable Harborview area of Shelter Island, this modern farmhouse blends luxury, comfort, and coastal living. Just 0.2 miles from a private waterfront association, enjoy easy access to kayaking and the beach. Set on a beautifully landscaped half acre, the home is designed for seamless indoor-outdoor living. The open-concept interior is flooded with natural light, featuring a chef’s kitchen that flows effortlessly to the dining and living areas, highlighting views of the backyard oasis. Outside, relax in the heated pool, outdoor shower, or firepit lounge, or entertain on the spacious deck with retractable awning and covered dining area. With five generous bedrooms, including primary suites on both the first and second floors, the home accommodates guests in style. The upstairs suite features a gas fireplace and covered balcony. The fully finished lower level includes a media room with theater seating, a versatile den or gym with yard access, and a fifth bedroom with a large hall bath. Step inside and start enjoying the best of Shelter Island living.

ⓘ Source: listings_history table (triggers on properties + properties_extension) + one-shot backfill from property_details.listing_events for pre-trigger history.

Climate risk First Street

• 🌊 Flood 1/10 Low FEMA zone X (unshaded) · 0% chance over 30 yrs
• 🔥 Wildfire 1/10 Low
• 🌡 Heat 5/10 Major 7 d/yr ≥90°F today · 19 d/yr by 30 yrs out
• 💨 Wind 8/10 Severe 80% chance of damaging wind over 30 yrs
• 🫁 Air quality 2/10 Low 2 unhealthy d/yr today · 2 by 30 yrs out

Taxation est. · year 1

• Rental income: $640,353
• − Mortgage interest: −$165,246
• − Property taxes: −$44,250
• − Insurance: −$14,750
• − Repairs & maintenance: −$51,228
• − Management: −$51,228
• − HOA: −$180
• − Depreciation: −$85,818
• Taxable income: $227,653
• Est. tax owed @ 24.0%: −$54,637
• After-tax cash flow: $206,421/yr

For passive investors: Depreciation is non-cash, so a rental often shows a tax loss while cash-flowing — sheltering income. Rental losses are passive: they offset passive income freely, and up to $25,000/yr can offset ordinary (W-2) income if you actively participate and your MAGI is under $100k (phasing out to $0 by $150k); unused losses carry forward. On sale, claimed depreciation is recaptured at up to 25%, and gains may owe capital-gains tax (a 1031 exchange can defer both). Figures are a year-1 estimate at your 24.0% rate — not tax advice; consult a CPA.

Condition & rehab AI · 12 photos

Good 80/100 Cosmetic rehab

This modern farmhouse in Shelter Island is in excellent condition with a good condition score of 80. It offers a spacious kitchen, well-maintained exterior, and a beautiful outdoor living area. The property is move-in ready with minimal repairs needed.

Value-add opportunities

• Both Landscaping improvements — Enhance curb appeal and outdoor living space
• Both Add smart home features — Improve convenience and energy efficiency
• Both Install a smart thermostat — Save on energy costs and improve comfort

Renovation cost estimate screening

Value-add ROI direction

• Both Landscaping improvements — Enhance curb appeal and outdoor living space ↑
• Both Add smart home features — Improve convenience and energy efficiency ↑
• Both Install a smart thermostat — Save on energy costs and improve comfort ↑

ⓘ Cost ranges are severity-bucket heuristics (US national rule-of-thumb). Get contractor quotes + a written scope before underwriting a rehab budget.

Schools (NCES district)

• District: Shelter Island Union Free School District
• NCES district ID: 3626640
• Math proficiency: 40% ▼ -15.00%
• Reading proficiency: 45% ▼ -15.00%
• Median HH income: $75,456
• Composite: 41.31/100
• National rank: #7365
• State rank: #546 of 755 in NY

Livability — Shelter Island

• Score: 60/100
• State rank: #998
• US rank: #19481

Category grades

Amenities F Commute F Cost of living F Crime A+ Employment A+ Housing C+ Health & safety D- User ratings A

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Shelter Island, NY
• City population: 3,279
• Population (ZIP): 2,858

Population outlook (Suffolk County) Hauer SSP2

• Today (2025): 1,505,262 people
• By 2030: 1,498,318 · -0.5%
• By 2040: 1,471,101 · -2.3%
• By 2050: 1,424,848 · -5.3%
• By 2075: 1,337,157 · -11.2%
• By 2100: 1,217,720 · -19.1%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Diverse neighborhood (Simpson 0.57)
• Race & ethnicity: White 62% Hispanic / Latino 21% Native American 15% Two or more races 7% Asian 6%
• Hispanic origin (detail): Mexican 16%
• Common ancestry: Italian 13% Romanian 5% Portuguese 1%
• Foreign-born: 15% · Canada
• Languages at home: 78% English-only · Spanish 18% Other Indo-European 3%

Political lean MEDSL · Suffolk

• 2024 margin: Lean R (+10.0) · D 45.0% · R 55.0%
• 2008→2024 swing: -16.0pp toward R · 2008: 6.0pp · 2024: -10.0pp
• All cycles: 2024: R+10.0 2020: R+0.0 2016: R+8.2 2012: D+2.9 2008: D+6.0

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▲ 1.97%
• Current HPI: 476.2348
• Rent YoY: —
• Metro: —
• State GDP YoY: ▲ 2.60%
• F500 in state: 92

Industry mix (Fortune 500 HQ in NY)

Industry	F500 HQs	Revenue
▸Financial Services	10	$950B
▸Consumer Goods	9	$162B
▸Insurance	4	$225B
▸Telecommunications	2	$144B
▸Pharmaceuticals	2	$112B
▸Media / Entertainment	2	$69B

Price history

+0.0% since first listed

2 events — show timeline

• 2026-04-08 Listed $2,950,000 OneKey® MLS as Distributed by MLS Grid
• 2026-04-02 Coming Soon $2,950,000 OneKey® MLS as Distributed by MLS Grid